


On Shocking, Pleasant Surprises

by dreamyemptysouls



Category: Homestuck
Genre: Crossdressing, M/M
Language: English
Status: Completed
Published: 2012-07-16
Updated: 2012-07-16
Packaged: 2017-11-10 02:22:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,099
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/461207
Author URL: https://archiveofourown.org/users/dreamyemptysouls/pseuds/dreamyemptysouls
Summary: <blockquote class="userstuff">
              <p>Your name is Jake English, and you really don't know how you got yourself in this situation.</p>
<p>For a while now, you've doubted of how well your good pal Dirk had raised himself in the absence of any other human stimuli, but it turns out the internet has probably taught him more than enough.</p>
            </blockquote>





	On Shocking, Pleasant Surprises

**Author's Note:**

> For [Jonah](http://jonahime.tumblr.com), who requested for crossdressing Dirk/Jake, and I tried my best to comply.
> 
> This is awful, I know. Two more requests and I'll ask for the last deadline to Birdbert.

Your name is Jake English, and you really don't know how you got yourself in this situation.

For a while now, you've doubted of how well your good pal Dirk had raised himself in the absence of any other human stimuli, but it turns out the internet has probably taught him more than enough. 

Proof number one is the high-couture, frilly dress he is wearing right now, bodice clinging rather snugly to his narrow, skinny frame, folds upon folds of the lacy poufy fabric of his skirt going around his bare, shapely legs.

You're not sure of how to react to his current dress code, but your body seems to have a very set response to this kind of vision regardless, and the blush spreading across your face, blood pooling at the most inconvenient of places, are making your mood embarrassingly obvious.

Not that he seems to mind. You haven't been in the same place as him for too long - and every moment has been filled with all too many surprises, all of them outrageous, most of them pleasant - but you've learned to recognize his smug smirks when you see them, and you believe he's presenting you with a modest, tentative version of one right now, shyly cast downwards. You wonder why it took him so long to show you this part of him. You've certainly seen him doing and liking positively weirder stuff, alone or when he was with you, and you were pretty alright past the initial shock and befuddlement.

So... what is holding him back now?

His sheepishness is new, as is the way he casually snaps the elastic sliding from his garter to the pastel thigh highs, but he seems encouraged by your reactions, and sure of how this is affecting you all the same. He looks up at you, through the pointy, sentient shades, and his smirk is definitely bigger now.

"Okay, English. You've been standing there gaping like a bespectacled fish out of the water for a little too long, don't ya think? You like what you see. I can tell that much. So maybe, and I am just venturin' a guess here, you might want to come closer too."

You open your mouth immediately after, hoping to have some actual words waiting to be said, but the gurgle you let out is not intelligent at all, making your face feel warmer and him actually chuckle now. He nudges his shades to the tip of his nose, orange eyes focused on you, and you see him raise his eyebrows in a perfect curve, whole body shifting from his kneeling position on the soft bed, your lusii sheets, to sitting on the edge of it, legs spread not suggestively at all, flashing you bits of soft looking, delicate underwear. You finally see what he has covering his feet too, pointedly dangling from the bed, and sweet goodness, are those your trekking boots? They look surprisingly rather well with the rest of his ensemble, and you feel like you've just forgotten how to breathe.

"Eloquently put, bro. Now shhh, just come."

And despite this display of confidence, you see his half-smile falter a little when you take a little too long to comply, expression still agape and paralyzed, your thoughts slowly processing themselves into actual actions. You see him falter and this is the beacon your brain needs to help you stumble forward, in panic and in a rush to please, fall on your knees before him and clumsily, gracelessly, mesh your mouths together in a searing, sloppy kiss.

Well, to be fair, none of you are THAT experienced in this kissing business, but you've gotten better, with time and after many tries. He holds you, his arms tightly knit around your shoulders, across your back, legs wrapped around your middle, the folds of his skirt swallowing your waist, and he moves his lips against yours rather expertly, the smirk always there, groaning low and warm as he brushes his tongue past your lips, over your teeth.

You whine shamelessly, begging him to coax you into a deeper kiss, inviting him in and swirling your own tongue around his, pressing yourself flush into his embrace. As for your hands, you know little of where to put them, but he helps you with that too, bending here and there as if nudging the strings he tied to your hands to their rightful place, fingers fumbling down his back, stroking the fabric and the straps and the lace, till they finally rest over the skirt, on the swell of his ass, squeezing it till he sighs.

And he does sigh, body going slack after grinding against you, making all of this realer and hotter and so much better. He falls on his back, making the mattress squeak while you follow close behind, settling between his legs, holding and pulling him closer to you, and you feel how hard he is, as you are, as he rolls his hips on yours again.

You can't possibly imagine not kissing him right now, and you smear your mouth to his with eagerness once more, whimpering with every motion of his body crashing on yours, every rustle of his skirt moving over you. Your hands fumble again, shakily seeking more contact, and you make them slip past the fabric, trailing up the thigh highs, the soft skin of his thighs, his panties, and gosh, you had never touched silk before in your whole life, and the strain of it over his hard dick makes you moan and tremble all over. You feel him mirror your reactions, but it probably has something to do with how your hand moves over him right now, tugging and squeezing through the silk.

The kiss becomes frenzied now, nothing more than frantic motions, mingled moans and his tongue still wrestling yours, and the two of you pull away when your lungs run out of air, when your glasses and shades start clacking too hard.

Bent over him on your knees, you still hear him pant as he reaches out to take off his shades and then your glasses, while you diligently leave a trail of kisses down his neck. Only then do you notice how your lips are leaving blue marks on his skin, and looking up at his face, deliciously red and eyes ablaze, you see how there's smudged cerulean lipstick all over his mouth. Oh...

"J-jesus flipping Christ, Dirk..." you splutter, choked up, diving in again to kiss between his collarbones, where the skin is tender and pulsing. “Are you trying to m-make this old heart stop with all this set up, p-pal? I very much b-believe you are..."

You hear him laugh harder now, even if he still sounds strangled, moaning in between breaths as you lick and nip on his chest, along the edge of the dress, your hands unrelenting, ever amazed at the texture of silk on boner. His hands are on your hair, gripping tightly (he never lets you do the same to his: it has to remain flawless at all times), and he pushes your face to his, lips moving to trail the shell of your ear.

"You are actually p-pretty fucking easy to figure out, English. I knew you'd love the dress. Sorry if it's the most "girl" that can come from me..."

And you feel there's something poignant in this, something you should dismiss, clear up, but he's kissing you again, unrestrained, and in between sloppy pecks he commands you to undress, but not completely. You are completely lost.

Your boots are the first to go, but you can't focus enough to toe off your socks, so they stay. With his hands moving to your chest, you struggle out of your jacket and then your shirt, giving him room to roam over taut muscle, rough, weathered skin. When his hands are over your crotch, cupping the evident bulge there, and his kisses all over your stomach, your hands fumble to unbuckle your belt and pry your shorts open, watching them and your boxers pool around your knees.

His hands go to your dick, his expression gone mellow, and he pumps it slowly, brushing the precum pooling there over the tip, watching you fall on top of him again, sighing against his neck. You're shameless about thrusting into his grip, moaning as your trail of kisses moves downwards, and he only relents his hold on you when you settle once more between his legs, burying your face deep inside the folds of his skirt just to nuzzle at his clothed erection, tracing it with your mouth.

Oh, the sounds he makes!, and you hum against him, working your tongue up and down, watching the precum and your saliva seeping through the silk before pulling the panties down with careful fingers. You're both impossibly hard, too far gone to ask for anything but release, and so you take him to the hilt, having learnt how to suppress your gag reflex for occasions such as this, bobbing your head between his legs, lost in his scent, his moans, in the frenzied rustling of his skirt around you. One hand grips his thigh, keeping him in place, but the other travels down to your own aching dick, and you try to make the two of you move together, pace yourselves in synchrony, so you can hear his moans when you open your mouth, feel him tremble, heels digging on your back as you squeeze your own dick.

Lost as you are, it doesn't take too long for you to clamber to the edge, and once your movements become more erratic, faster, more eager, you hear him groan your name and feel him spill into your mouth, your cue to following suit, coming into your hand. You collapse against him, peppering his softening dick and his inner thighs with sweet kisses and short, ragged puffs of breath, as you listen to him pant hard, wrapping his legs around your back, threading your hair with his calloused, expert hands.

When you finally resurface, reaching out for a wet towel (essential to every adventurer) to clean yourselves, you lazily snuggle against him, and take your sweet time studying how he looks, chin in hand. And goodness, you had just regained your breath, why did he have to go and take it away from you again? The lipstick is more smeared than ever, freckles standing in sharp relief against the red of his face, eyes still glowering, mouth parted as he pants, making the straps holding his corset together tense and relax with him.

He looks down at you smiling, and you clamber on top of him, kissing him slowly on the lips once more. You stop only to sit up, to pull his smaller frame to snuggle against you, whispering more to his ear.

"Gosh, Dirk you... look absolutely gorgeous, you know? Well, you ARE absolutely gorgeous, even when... hm, may I?"

He raises his eyebrows at you again, but allows you to work carefully to remove his boots, the thigh highs and the garters, the rest of the panties, your own socks and undergarments, and then finally the dress. You are bit clumsy with the straps, shaky around the fabric that still smells of sex, and passion, and of you, but it comes off anyway. You hold it almost religiously, like a relic you have discovered in one of the most sacred tombs in this island, and as you place it next to you, you turn to face Dirk with a wide grin.

"We are certainly making use of that in the future, mark my fucking words, but... frankly, my dear... I don't give a damn whether you're a girl, or a boy, or either. You're amazing, and you're beautiful, and you'd be a major asshole anyway. And I love you for all that."

You have the pleasure of having him look wide-eyed at you through your little speech, right before his expression breaks into one of pure tenderness and he chuckles, nuzzling shamelessly at the curve of your neck.

"You are such a fuckin' dork, English, I can't even... I don't know how to deal with you. But thank you. I love you too."

You giggle, because it tickles just as much as it feels good, and you guess more laughter it's what the both of you need after everything. Touch starved, no matter how many times you succumb to each other, you eventually lay across the bed once more, him held tight in your arms, lazily inviting slumber to take over.


End file.
